NP-MRD: Showing NP-Card for glandin (NP0282312)

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Record Information

Version

2.0

Created at

2022-09-09 09:05:56 UTC

Updated at

2022-09-09 09:05:57 UTC

NP-MRD ID

NP0282312

Secondary Accession Numbers

None

Natural Product Identification

Common Name

glandin

Description

Dinoprost, also known as enzaprost or PGF2A, belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Thus, dinoprost is considered to be an eicosanoid lipid molecule. Dinoprost is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In humans, dinoprost is involved in mefenamic acid action pathway. glandin is found in Cervus nippon, Gersemia fruticosa, Larix sibirica and Mus musculus. glandin was first documented in 2013 (PMID: 23807981). A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004221603162D          

 34 34  0  0  1  0            999 V2000
   -0.5662    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1483    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6332    8.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4178    8.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4617    7.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5894    9.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748    6.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9763    9.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0428    4.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    6.0577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9033    5.9808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1496    5.6452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4553    5.3677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2358    4.8247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1478   10.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    6.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2758    5.4539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    4.2727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5347   11.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9324   10.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0201    8.6988    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6771    7.0848    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206    4.8202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351    6.8827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    5.2327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7001    6.1943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1928    6.4691    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9046    4.6758    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4656    5.1204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 13 12  2  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  1  0  0  0
 17 13  1  6  0  0  0
 17 16  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 14  1  0  0  0  0
 19 17  1  0  0  0  0
 20 11  1  0  0  0  0
 15 21  1  1  0  0  0
 18 22  1  1  0  0  0
 19 23  1  1  0  0  0
 24 20  2  0  0  0  0
 25 20  1  0  0  0  0
 26  4  1  0  0  0  0
 27  7  1  0  0  0  0
 28 12  1  0  0  0  0
 29 13  1  0  0  0  0
 15 30  1  1  0  0  0
 16 31  1  6  0  0  0
 17 32  1  1  0  0  0
 18 33  1  6  0  0  0
 19 34  1  6  0  0  0
M  END

     RDKit          3D

 59 59  0  0  0  0  0  0  0  0999 V2000
    8.0176    0.8416   -1.6874 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9036   -0.3936   -0.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5916   -0.4315   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4078   -0.4252   -1.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -0.4671   -0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9002   -0.4635   -1.0481 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9094    0.7445   -1.7539 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -0.5077   -0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5097   -0.3687   -0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7535   -0.3832    0.2235 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6191   -0.5096    1.6977 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6707   -1.3456    2.1598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884    0.8739    2.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9669    1.7760    1.1439 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7440    2.8928    1.4062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4276    0.9501    0.0186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9051    0.8789   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7146    0.3495    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4811   -0.7186    0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6582   -1.5473   -0.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1089   -1.5699   -0.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7357   -0.2748   -1.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7714    0.7241   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2534    1.8501   -0.2658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3855    0.4147    1.0721 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5887    0.6428   -2.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1140    1.0563   -1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4703    1.7009   -1.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6994   -0.3813   -0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9658   -1.2761   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5892    0.4444    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5707   -1.3966    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4488   -1.3827   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4286    0.4543   -1.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1408   -1.3160    0.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1193    0.4750    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8868   -1.3184   -1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167    1.4572   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8738   -0.6535    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4012   -0.2186   -1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4577   -1.1637   -0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2892   -1.0023    2.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4687   -2.2837    1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6143    0.9007    3.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1415    1.0746    2.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0581    2.1777    0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407    3.5154    0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0103    1.3813   -0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761    0.3534   -1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2831    1.9350   -0.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7426    0.8122    1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0718   -1.0556    1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3602   -2.6166   -0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0555   -1.2566   -1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2719   -2.2812   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7261   -2.0387   -0.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2533    0.1454   -2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7963   -0.4743   -1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1000    0.6991    1.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 25  1  0
 23 24  2  0
 19 18  2  0
 18 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
 10 16  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
 18 51  1  0
 17 49  1  0
 17 50  1  0
 16 48  1  6
 14 46  1  6
 15 47  1  0
 13 44  1  0
 13 45  1  0
 11 42  1  6
 12 43  1  0
 10 41  1  6
  9 40  1  0
  8 39  1  0
  6 37  1  6
  7 38  1  0
  5 35  1  0
  5 36  1  0
  4 33  1  0
  4 34  1  0
  3 31  1  0
  3 32  1  0
  2 29  1  0
  2 30  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END


  Mrv1572004221603162D          

 34 34  0  0  1  0            999 V2000
   -0.5662    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1483    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6332    8.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4178    8.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4617    7.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5894    9.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748    6.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9763    9.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0428    4.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    6.0577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9033    5.9808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1496    5.6452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4553    5.3677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2358    4.8247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1478   10.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    6.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2758    5.4539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    4.2727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5347   11.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9324   10.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0201    8.6988    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6771    7.0848    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206    4.8202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351    6.8827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    5.2327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7001    6.1943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1928    6.4691    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9046    4.6758    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4656    5.1204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 13 12  2  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  1  0  0  0
 17 13  1  6  0  0  0
 17 16  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 14  1  0  0  0  0
 19 17  1  0  0  0  0
 20 11  1  0  0  0  0
 15 21  1  1  0  0  0
 18 22  1  1  0  0  0
 19 23  1  1  0  0  0
 24 20  2  0  0  0  0
 25 20  1  0  0  0  0
 26  4  1  0  0  0  0
 27  7  1  0  0  0  0
 28 12  1  0  0  0  0
 29 13  1  0  0  0  0
 15 30  1  1  0  0  0
 16 31  1  6  0  0  0
 17 32  1  1  0  0  0
 18 33  1  6  0  0  0
 19 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0282312

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCCC(O)=O)=C(/[H])C[C@@]1([H])[C@@]([H])(O)C[C@@]([H])(O)[C@]1([H])C(\[H])=C(/[H])[C@@]([H])(O)CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

> <INCHI_KEY>
PXGPLTODNUVGFL-YNNPMVKQSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.487

> <EXACT_MASS>
354.240624195

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
40.855742182967404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
2.6110544173333317

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.513964334215405

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.355294048784039

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6263153076120291

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
100.4707

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glandin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -1.057  10.538   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.277  11.308   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.610  10.538   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.515  15.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.980  15.683   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.944  11.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.195  13.701   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.300  17.189   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.278  10.538   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.340  12.670   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.156  18.220   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.945  10.538   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.279  11.308   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.280   8.686   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.612  11.308   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.019  11.164   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.613  10.538   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.050  10.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.774   9.006   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.476  19.726   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.612  12.848   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      13.581  10.181   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.629   7.976   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.331  20.757   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      12.941  20.202   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       9.371  16.238   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       8.731  13.225   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       6.945   8.998   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       8.279  12.848   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.612   9.768   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      12.507  11.563   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       9.693  12.076   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      12.889   8.728   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       8.336   9.558   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    6                                                       
CONECT    4    5    7   26                                                  
CONECT    5    4    8                                                       
CONECT    6    3    9                                                       
CONECT    7    4   10   27                                                  
CONECT    8    5   11                                                       
CONECT    9    6   15                                                       
CONECT   10    7   16                                                       
CONECT   11    8   20                                                       
CONECT   12   13   15   28                                                  
CONECT   13   12   17   29                                                  
CONECT   14   18   19                                                       
CONECT   15    9   12   21   30                                             
CONECT   16   10   17   18   31                                             
CONECT   17   13   16   19   32                                             
CONECT   18   14   16   22   33                                             
CONECT   19   14   17   23   34                                             
CONECT   20   11   24   25                                                  
CONECT   21   15                                                            
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   20                                                            
CONECT   25   20                                                            
CONECT   26    4                                                            
CONECT   27    7                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   19                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

View in JSmol

Synonyms

Value	Source
(+)-Prostaglandin F2a	ChEBI
(5Z,13E)-(15S)-9alpha,11alpha,15-Trihydroxyprosta-5,13-dienoate	ChEBI
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid	ChEBI
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oic acid	ChEBI
9a,11a-PGF2	ChEBI
Amoglandin	ChEBI
Cyclosin	ChEBI
Dinoprosta	ChEBI
Dinoprostum	ChEBI
Enzaprost	ChEBI
Enzaprost F	ChEBI
L-PGF2-alpha	ChEBI
L-Prostaglandin F2-alpha	ChEBI
Panacelan	ChEBI
PGF2a	ChEBI
PGF2alpha	ChEBI
Prostaglandin F2a	ChEBI
Prostin F 2 alpha	ChEBI
Protamodin	ChEBI
U 14583	ChEBI
(5Z,9alpha,11alpha,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dienoate	Kegg
Prosmon	Kegg
(5Z,13E)-(15S)-9a,11a,15-Trihydroxyprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-9a,11a,15-Trihydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-9alpha,11alpha,15-Trihydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-9Α,11α,15-trihydroxyprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-9Α,11α,15-trihydroxyprosta-5,13-dienoic acid	Generator
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoate	Generator
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oate	Generator
L-PGF2-a	Generator
L-PGF2-Α	Generator
L-Prostaglandin F2-a	Generator
L-Prostaglandin F2-α	Generator
PGF2Α	Generator
Prostin F 2 a	Generator
Prostin F 2 α	Generator
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dienoate	Generator
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dienoic acid	Generator
(5Z,9alpha,11alpha,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dienoic acid	Generator
(5Z,9Α,11α,13E,15S)-9,11,15-trihydroxyprosta-5,13-dienoate	Generator
(5Z,9Α,11α,13E,15S)-9,11,15-trihydroxyprosta-5,13-dienoic acid	Generator
Dinoprost	ChEBI
(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(e,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate	Generator
9alpha,11beta-PGF2	MeSH
Prostaglandin F2	MeSH
9alpha,11beta PGF2	MeSH
F2 alpha, Prostaglandin	MeSH
F2alpha, Prostaglandin	MeSH
Prostaglandin F2 alpha	MeSH
Prostaglandin F2alpha	MeSH
alpha, PGF2	MeSH
Estrofan	MeSH
PGF2	MeSH
PGF2 alpha	MeSH

Chemical Formula

C₂₀H₃₄O₅

Average Mass

354.4870 Da

Monoisotopic Mass

354.24062 Da

IUPAC Name

(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

Traditional Name

glandin

CAS Registry Number

Not Available

SMILES

[H]\C(CCCC(O)=O)=C(/[H])C[C@@]1([H])[C@@]([H])(O)C[C@@]([H])(O)[C@]1([H])C(\[H])=C(/[H])[C@@]([H])(O)CCCCC

InChI Identifier

InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

InChI Key

PXGPLTODNUVGFL-YNNPMVKQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cervus nippon	LOTUS Database	35616633
Gersemia fruticosa	LOTUS Database	35616633
Larix sibirica	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Long-chain fatty acid
Hydroxy fatty acid
Cyclopentanol
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:15553 )
prostaglandins Falpha (CHEBI:15553 )
Prostaglandins (C00639 )
Prostaglandins (LMFA03010002 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.11	ALOGPS
logP	2.61	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	100.47 m³·mol⁻¹	ChemAxon
Polarizability	40.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB12789

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00639

BioCyc ID

5Z13E-15S-9-ALPHA11-ALPHA15-TRIHY

BiGG ID

Not Available

Wikipedia Link

Dinoprost

METLIN ID

Not Available

PubChem Compound

5280363

PDB ID

Not Available

ChEBI ID

15553

Good Scents ID

Not Available

References

General References

Bojinova S, Porozhanova K: [The use of prostaglandin F2alpha (Prostin 15M) for terminationof second trimester pregnancy]. Akush Ginekol (Sofiia). 2013;52(2):53-5. [PubMed:23807981 ]
LOTUS database [Link]

Showing NP-Card for glandin (NP0282312)

MOL for NP0282312 (glandin)

3D MOL for NP0282312 (glandin)

3D SDF for NP0282312 (glandin)

3D-SDF for NP0282312 (glandin)

PDB for NP0282312 (glandin)

3D PDB for NP0282312 (glandin)

SMILES for NP0282312 (glandin)

INCHI for NP0282312 (glandin)

Structure for NP0282312 (glandin)

3D Structure for NP0282312 (glandin)